Most of our bike tours are designed to incorporate historical sites into your vacation. Don’t worry if you are not a history buff, it will not feel like a college class! These are beautiful and fun destinations, and you can choose how much you want to interact with the history.

Not just looking at some old buildings!

Not only will you experience unique and historic lodging on our Inn-to-Inn bike tours, our bike tour destinations have you interacting with history in a way most people have never tried … from a bicycle seat. Many of our bike tours incorporate guided battlefield tours, routes through our National Parks, visits to historic landmarks and cycling through National Historic Districts.

For a place to be deemed a National Historic District, it not only has to be old, it also must be historically or culturally significant. These National Historic Districts protect and preserve structures, sites, and public ways that reflect an important piece of history, architecture, archaeology, engineering or culture.

Historic Districts are created and protected because they possess a concentration of buildings, structures, objects or sites that are linked either historically or aesthetically.

What does a Historic District look like?

Historic Districts are not just specific sections of a city, either. Historic Districts are everything from a residential area with several buildings constructed in the same distinct style, to a downtown business district that preserves the buildings that aided the town’s early development. Other examples of Historic Districts include college campuses, large estates or farms, villages and industrial complexes.

There is a Historic District near you!

More and more neighborhoods have become candidates for historic preservation, and more than 2,300 historic districts dot the United States today.

So, what Historic Districts do you visit?

All this talk about what a Historic District is, and what makes them so cool & unique … how about we let you know what bikes tours feature these special places!

We’ve pulled together a brief listing of some of our favorite historic districts, to help you decide which bike tour to choose.

Cycle back through Savannah’s past

Did you know that Savannah is the largest National Historic Landmark District in the United States?

Containing more than twenty city squares filled with museums, churches, mansions, monuments and famous forts of the Revolutionary & Civil War eras, our cycling journey through this impressive historic district will transform even the most uninterested into history fanatics.

Savannah’s recognition as a National Historic Landmark District is significant, not only because of it’s stunning 18th & 19th century architecture, but also due to the district’s unique grid plan laid out during its founding.

In 1733, Gen. James E. Oglethorpe established the British colony of Georgia, and quickly went to work creating one of the most intricate town plans. The town was laid out in a grid pattern, with 24 squares that focused each “neighborhood”, or ward. These squares existed as the center of each ward, and included all the civic and educational pillars of that ward (schools, court houses, etc.). Today Savannah retains much of this plan, which is based on wards, squares, and “trustee lots.”, and most of the original squares remain.

Each year, the Savannah Historic District attracts millions of visitors, who enjoy its eighteenth- and nineteenth-century architecture and green spaces. Stroll down cobblestone streets, visit historic squares filled with old live oaks dripping with Spanish moss, discover grand mansions and amazing ironwork. See why we say there is no other city quite like Savannah.

Luxe Leisure on Jekyll Island

Whether lounging by the pool or strolling the private beach, when you watch the fading sun cast brilliant hues of blues and reds over the Atlantic at Jekyll Island Club Resort, you will be in awe. Transported to a different era, this is the same view that kept the famous and elite families like the Vanderbilts and Rockefellers spending their summers here, year after year.

One recognized as “the richest, most inaccessible club in the world”, nowadays this elegant island escape is one of the largest ongoing restoration projects in the southeastern United States. The club itself was placed on the National Register of Historic Places in 1972, and it 1979 the former club grounds was awarded Landmark status by the National Park Service. The Jekyll Island Club National Historic Landmark is comprised of 240-acres of the original club grounds and 34 historic structures that exist there, and is a true testament of it’s importance to American History.

Seaport Towns on the Chesapeake

There certainly isn’t a lack of bayside sights and culture on our Maryland’s Chesapeake Bay Bike Tour. Not only do you experience four days of very moderate cycling on country roads, and lots of seafood … but you will also get to experience TWO National Historic Districts along the way!

Oxford and St. Michaels are both located in Talbot County, Maryland, and both have a long history as important and strategic port towns on the Chesapeake Bay. After visiting, you are sure to agree that Talbot County is a true historic gem of the Chesapeake’s Eastern Shore!

A History of Seafaring and Shipping

Cycling through Oxford, Maryland’s Historic District, you will be riding through one of the state’s earliests towns! Established in 1683, Oxford quickly gained prominence as an international shipping center up until the American Revolution. During this rise, Annapolis and Oxford stood as the only ports of entry for the entire Maryland territory. The American Revolution, however, marked the end of Oxford’s age of prosperity.

It wasn’t until after the Civil War that Oxford was put on the map again. The 19th century saw the completion of vital railroad tracks, and a booming oyster industry.

Although Oxford’s history begins in the 17th century, there are no structures remaining from the 17th or 18th centuries. Oxford is primarily defined by structures erected between 1875 and 1910.

Its quiet charm, fresh air, summer breezes, and clean water provide a haven from the hustle and bustle of city life for boaters, weekend visitors, and summer residents.

Within the last ten years, St. Michaels has experienced a new Renaissance of sorts, and nearly 90 percent of the district has been restored or rehabilitated.

Many of these magnificently restored structures were originally constructed as a result of the town’s ship building prosperity in the late 19th century. As many as six shipbuilders were active in or near the town itself by the War of 1812. In those days, the most popular ship built here were narrow, fast schooners, today known as the Baltimore Clipper.

Established in 1972, the St. Michaels Historic District was created to safeguard its rich heritage by

Historic Harpers Ferry

Harpers Ferry Historic District comprises about one hundred historic structures and sites in Harpers Ferry, West Virginia! Most known for its participation in the Civil War, the town of Harpers Ferry was a battlefield between Union and Confederate Soldiers.

The District encompasses portions of Harpers Ferry that are not included in Harpers Ferry National Historical Park, like the large numbers of early 19th-century houses built by the United States Government for the workers at Harpers Ferry Armory. The majority of building you will see in date from 1800 through the Civil War period.

Situated on the Potomac and Shenandoah Rivers, on the border of Maryland, Virginia and West Virginia, the town is located on a low-lying flood plain created by the two rivers surrounded by hills. In the late 19th century, a number of Victorian and Federalist-style houses were built on higher ground. These more elegant mansion-style homes received famous guests, like Mark Twain, Alexander Graham Bell and Woodrow Wilson.

With its rich history and pivotal role in American History, the Historic District has preserved an essentially intact 19th century town.

Hunting & Horses in Middleburg

Established in 1787 by a Revolutionary War officer, Middleburg Virginia was a strategic coach stop and relay station due to it’s central location.

The Civil War drew troops into this area, and the town saw frequent Civil War cavalry action.

One of the more notable buildings in Middleburg’s Historic District, is the Red Fox Inn & Tavern. Built in 1728, this structure is the oldest building in town, and is listed individually on the National Register of Historic Places. Of its many contributions, some of it’s more interesting ones are serving as headquarters and hospital for the Confederate Army during the Civil War, and also serving as the site of President Kennedy’s 1961 press conference.

Although Middleburg played a big role throughout the Civil War, by the 20th century, it assumed a new identity as a hunting and equestrian center. Middleburg prospered and grew in reputation as the nation’s foremost area for fox hunting, Thoroughbred breeding, and horse racing.

Now-a-days this town is thought of as the physical and psychological heart of Northern Virginia’s hunt country. This small town of about 600 residents has held undisputed claim to this title since the early 20th century when wealthy sporting enthusiasts and their horses and hounds claimed the town and its lush rolling countryside as their own.

Historic Crossroads in Leesburg

With a rich history spanning three centuries, Leesburg, Virginia was originally settled by Europeans around the late 1730s. Tidewater planters began arriving from the South and East, establishing large farms and plantations around the countryside.

Many of Virginia’s First Families also arrived in Leesburg around this time. Then called, George Town, Leesburg was an important commercial crossroads, sitting in the intersection of the Old Carolina Road and the Potomac Ridge Road.

In 1757, the town was officially names and the Loudoun County Courthouse was erected, and Leesburg has served as the county seat ever since.

Preserving a nostalgic, small-town character, the Leesburg Historic District is centered around a park-like town square containing the 1895 Classical Courthouse and a Greek Revival Academy building.

Many buildings in the historic district date from Leesburg’s 18th-century development, and include some log structures. Interspersed among the Georgian and Federal buildings in the Historic District, however, are many buildings from the second half of the 19th century, including the Italian Villa residence built in 1857.

Just a mear 33 miles outside of our nation’s capital, Leesburg has undergone considerable growth and development over the last 30 years. It has transformed from a rural, piedmont town to a suburban “bedroom” community for commuters working in Washington, D.C..

Walking along the brick sidewalks or cycling its historic avenues, with the muted Colonial color palette, you will be experiencing three centuries of American and architectural history.

Shepherdstown West Virginia

Founded in 1762 as Mecklenburg, Shepherdstown is the oldest town in West Virginia. Sadly, though, no structures are known to exist from the period of time before the town became known as Shepherdstown.

The Shepherdstown Historic District was created in 1961, due to its significance to American history. It not only was the staging ground for many notable historic events, like the first demonstration of the steamboat by James Rumsey in 1787, but it also played an important role throughout the Civil War.

During the Civil War, Shepherdstown was in a pivotal position! Confederate forces burned the covered bridge over the Potomac in 1861, cutting off precious access into and out-of Shepherdstown. Confederate troops used the nearby Pack Horse Ford (shallow river crossing) to travel to and from the bloody Battle of Antietam. In the wake of Antietam, the entire town became a Confederate field hospital. Public and residential buildings alike were used as military hospitals for the wounded. Later, Union troops occupied the town to preserve the Baltimore and Ohio Railroad link to the west.

Never having experienced a significant population explosion, Historic Shepherdstown retains much of its original charm. Small shops and restaurants line its lamplit streets, and contribute to the small-town historic feel.